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Key West is a city and an island of the same name near the southernmost tip of the Florida Keys in Monroe County, Florida, United States. The city encompasses the namesake island, the part of Stock Island north of US-1 (the Overseas Highway) (east), Sigsbee Park (north, originally known as Dredgers Key), Fleming Key (north), and Sunset Key (west, originally known as Tank Island). Nearby Key Haven (northeast), the part of Stock Island south of US-1 (east) and Wisteria Island, better known as Christmas Tree Island (northwest), are in unincorporated Monroe County. Both Fleming Key and Sigsbee Park are part of the NAS Key West and are inaccessible by civilians. Key West is the county seat of Monroe County.

Key West is known as the Southernmost City in the Continental United States. It is also the southern terminus of U.S. Route 1, State Road A1A and the East Coast Greenway.
Key West is 129 miles (207 km) southwest (229.9 degrees) of Miami, Florida, (about 160 driving miles) and 106 miles (170 km) north northeast (21.2 degrees) of Havana, Cuba.Cuba, at its closest point is 98 statute (85 nautical) miles due south.
Key West is a seaport destination for many passenger cruise ships. The Key West International Airport provides airline service. Hotels and guest houses are available for lodging.
Naval Air Station Key West is an important year round training site for naval aviation due to the superb weather conditions. It is also a reason the city was chosen as the Winter White House of President Harry S. Truman.
The central business district primarily comprises Duval Street, and includes much of the northwest corner of the island along Whitehead, Simonton, Front, Greene, Caroline, Eaton Streets and Truman Avenue.
The official town motto is "One Human Family" and is also the capitol of the "Conch Republic" The Conch Republic is a micronation declared as a tongue-in-cheek protest secession of the city of Key West from the United States on April 23, 1982. It has been maintained as a tourism booster for the city since.
While the protest that sparked its creation, and others which have occurred periodically since then have been described by some as "tongue-in-cheek", they were motivated by frustrations over genuine concerns. The original protest event was motivated by a U.S. Border Patrol roadblock and checkpoint which greatly inconvenienced residents and was detrimental to tourism in the area.
Although the Conch Republic is not, and never was, a real secessionist movement, many in Key West continue to identify with the concerns that motivated the original protest against what they view as an "unresponsive" central government taking action without considering all of the implications. At least three related protests have taken place subsequent to the original incident.
The Conch Republic celebrates Independence Day every April 23 as part of a week-long festival of activities involving numerous businesses in Key West. The organization - which appears to be operated as a private business by its "Secretary General", Peter Anderson - is a key tourism booster for the area. It also issues its own souvenir passports and postage stamps

History Overseas by Railroad!
Key West was relatively isolated until 1912 when it was connected to the Florida mainland via Overseas Railway extension of Henry M. Flagler's Florida East Coast Railway (FEC). Flagler created a landfill at Trumbo Point for his railyards. The Labor Day Hurricane of 1935 destroyed much of the railroad, and killed hundreds of residents, including around 400 World War I veterans who were living in camps and working on federal road and mosquito-control projects in the Middle Keys. The FEC could not afford to restore the railroad.
The United States Federal Government then rebuilt the rail lines as an automobile highway, completed in 1938, which became an extension of United States Highway 1. The portion of US 1 through the Keys is called the Overseas Highway. Franklin Roosevelt toured the road in 1939.

The Winter White House
Truman Annex

Several Presidents have visited Key West. Harry Truman visited for 175 days on 11 visits during his Presidency and visited several times after he left office
Key West was in a down cycle when Franklin D. Roosevelt visited in 1939. The build up of military bases on the island occurred shortly thereafter.
In addition to Truman, Dwight D. Eisenhower stayed in Key West following a heart attack. In November of 1962, John F. Kennedy visited Key West a month after the resolution of the Cuban Missile Crisis. Jimmy Carter held a family reunion in Key West after leaving office.

Famous Sloppy Joe's Bar
The Silver Slipper dance hall adjacent to Sloppy Joe's, painted in the 1930s by Waldo Peirce
The Ernest Hemingway House, a popular tourist attraction in Key West.
One of the over 50 polydactyl cats that live at the Hemingway house. This particular cat has 7 (2 extra) toes on each paw.
A typical Cuban mix that can be found in many cafés and restaurants in and around the island
Ernest Hemingway and Tennessee Williams
Numerous artists and writers have passed through Key West but the two most associated with the island are Ernest Hemingway and Tennessee Williams.

Ernest Hemingway
Legend has it that Ernest Hemingway wrote A Farewell to Arms while living above the show room of a Key West Ford dealership at 314 Simonton Streetwhile awaiting delivery of a Ford Roadster purchased by the uncle of his wife Pauline in 1928.
Hardware store owner Charles Thompson introduced him to deep sea fishing. Among the group that went fishing was Joe Russell (also known as Sloppy Joe). Russell was reportedly the model for Freddy in To Have and Have Not. Portions of the original manuscript were found at Sloppy Joe's Bar after his death. The group had nicknames for each other and Hemingway wound up with "Papa".
Pauline's rich uncle Gus Pfeiffer bought the 907 Whitehead Street house in 1931 as a wedding present. Legend says the Hemingways installed a swimming pool for $20,000 in the late 1930s (equivalent in 2006 to $250,000). It was such a high price that Hemingway is said to have put a penny in the concrete saying "Here, take the last penny I've got!" The penny is still there.
During his stay he wrote or worked on: Death in the Afternoon, For Whom the Bell Tolls, The Snows of Kilimanjaro, and The Short Happy Life of Francis Macomber. He used Depression-era Key West as the locale for To Have and Have Not — his only novel set in the United States.
Pauline and Hemingway divorced in 1939 and Hemingway only occasionally visited while returning from Havana until his suicide in 1961.
The six or seven-toed polydactyl cats descended from Hemingway's original pet 'Snowball' still live on the grounds and are cared for at the Hemingway House, despite complaints by the U.S. Department of Agriculture in which the Key West City Commission exempted the home from a law prohibiting more than four domestic animals per household.

Tennessee Williams
Tennessee Williams first became a regular visitor to Key West in 1941, and is said to have written the first draft of A Streetcar Named Desire while staying in 1947 at the La Concha Hotel. He bought a permanent house in 1949 and listed Key West as his primary residence until his death in 1983. In contrast to Hemingway's grand house in Old Town, Williams home at 1431 Duncan Street in the "unfashionable" New Town neighborhood is a very modest bungalow. The house is privately owned and not open to the public. The Academy Award–winning film version of his "The Rose Tattoo" was shot on the island in 1956. The Tennessee Williams Theatre is located on the campus of Florida Keys Community College on Stock Island.
Williams had a series of rentals all over the U.S. but the only home he owned was in Key West.
Even though Hemingway and Williams were in Key West at the same time, they reportedly only met once -- at Hemingway's Cuba home Finca Vigia.

Cuban Presence
Key West is much closer to Havana than it is to Miami.
In 1890 Key West had a population of nearly 18,800 and was the biggest and richest city in Florida. Half the residents were said to be of Cuban origin and Key West regularly had Cuban mayors, including Carlos Manuel de Céspedes Father of the Cuban Republic, who was elected mayor in 1876. Cubans were actively involved in reportedly 200 factories in town producing 100 million cigars annually. José Martí made several visits to seek recruits for Cuban independence starting in 1891, and founded the Cuban Revolutionary Party during his visit to Key West.
The Battleship USS Maine sailed from Key West on its fateful visit to Havana, where it blew up, igniting the Spanish-American War. Crew men from the ship are buried in Key West and the Navy investigation into the blast occurred at the Key West Customs House.
Pan American Airlines was founded in Key West originally to fly visitors to Havana in 1926.
John F. Kennedy was to use "90 miles from Cuba" extensively in his speeches against Fidel Castro. Kennedy himself visited Key West a month after the resolution of the Cuban Missile Crisis.
Prior to the Cuban revolution of 1959, there were regular ferry and airplane services between Key West and Havana.
Key West was flooded with refugees during the Mariel Boatlift. Refugees continue to come ashore and on at least one occasion, most notably in April 2003, flew hijacked Cuban Airlines planes into the city's airport.

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The Florida Keys and Key West Video Travel Guide